Say Anything... (1989)

Ione Skye plays a high-school valedictorian on the verge of heading to England on a prestigious scholarship. This is especially thrilling to Skye's divorced father John Mahoney, who has always shared a special relationship with the girl, less father/ daughter than friend/ friend. When Skye begins dating irresponsible army brat John Cusack, her father despairs at her choice of an "underachiever." Pressured by her dad to break off the relationship, Skye spends the rest of the summer being pursued by the lovestruck Cusack, who does everything he can to win her back. Skye finally realizes there's more to life than perfection when her sainted father comes under the scrutiny of the IRS.